


Deck The Halls (And Place Your Bets)

by Ias



Category: Supernatural
Genre: Alternate Universe, Betting, Christmas, Fluff, M/M, Party
Language: English
Status: Completed
Published: 2012-12-25
Updated: 2012-12-25
Packaged: 2017-11-22 09:59:30
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,591
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/608569
Author URL: https://archiveofourown.org/users/Ias/pseuds/Ias
Summary: <blockquote class="userstuff">
              <p>Sam makes a bet with Dean that he can't find a roommate by the end of their oncoming Christmas party. Dean soon realizes this is easier said than done, but Sam knows something he doesn't.</p>
            </blockquote>





	Deck The Halls (And Place Your Bets)

**Author's Note:**

> My second piece written for the [Destiel Advent Calendar](http://destieladventcalendar.tumblr.com/). My first piece can be found [here](http://archiveofourown.org/works/595426).

Dean hated Christmas parties. The only good one he had ever gone to was when the lights on the Christmas tree overheated and caught fire. That had ended with half the guests fleeing into the back yard, where they had soon discovered that the swimming pool, while cunningly disguised by a fresh coat of ice and snow, was not solid enough to support a person’s weight. But according to Sam, laughing at other people’s misfortune wasn’t exactly the best way of getting into the holiday spirit, so Dean decided that he hated parties as a rule. 

Jess said that he just hadn’t been to the right one yet. Well, Dean thought that was bullshit, but he wasn’t going to tell her that. Cute little blonde she may be, but it hadn’t taken Dean long to find out that she had a mean right hook to go along with that cutting mind. And once she got a hold of an idea, she was not going to let it go until she succeeded or the world was ashes. 

Take, for example, this party. It was the last one that Sam and Dean would have while living in the same apartment; now that he and Jess were happily engaged, he’d be moving into a new place with her sometime in January. That also meant that it was possibly the last time Dean would ever be obligated to participate in this crap, and so Jess had made it her job to create the most ridiculous, over-the-top Christmas celebration that mortal minds could possibly conceive. 

She had been bustling around Sam and Dean’s apartment for the past week putting up decorations, and even worse she had managed to rope Sam into it. Typical. The two nerdy lovebirds had probably written a equations for the exact ratio of tinsel to be wrapped around every surface. They had a wreath on the outside and the inside of the door, for Christ’s sakes. Dean couldn’t even put his foot down without stepping on a Christmas ornament. 

“Seriously dude, I think I might be having a stroke,” Dean grumbled as Sam finished plugging in the last of the flashing Christmas lights. Jess stood back to admire their work, her hands on her hips. 

“Looks great, babe,” she said, standing on her toes to kiss Sam’s cheek as he slid his arm around her waist. 

“Could you not do that in front of me?” Dean groused. “Freakin’ lovebirds.”

“You’re so immature,” Sam said with a grin. “Hey, you never know. If you loosen up on that Scrooge impression you’ve got going on, maybe you’ll find a lovebird of your own.” 

“Especially with who’s coming,” Jess said, her smile turning more wicked. Dean was immediately suspicious. 

“What? Who’s coming?” he demanded. Sam just laughed. 

“Can we tell him?” he asked, his eyes bright.

Jess just shook her head, still grinning evilly at Dean. “Trust me, it will be worth the wait.” 

“Whatever. I don’t care.” Dean leaned back on the couch and crossed his arms over his chest. 

“Awww,” Jess cooed. “Your brother is so adorable when he’s sulking.” Dean threw a pillow at her. 

 

\---

 

The next day, Dean was maneuvering his way around the piles of wrapping paper which kept mysteriously appearing on the floor when Sam intercepted him in the living room. 

“So,” he said, leaning on the back of the couch. “First time living alone. You excited?” 

“Sammy, I am freakin’ thrilled,” Dean said with a grin, plopping down into the armchair and groping for the remote. To be honest, he wasn’t nearly as excited as he may have been leading Sam and Jess to believe, but he wasn’t about to ruin their big step with his own stupid feelings. “My first act as supreme ruler of the apartment will be to abolish pants and any food with leaves in it.” 

“You are actually a six-year-old,” Sam said, rolling his eyes as he sat down on the couch and propped his feet on the table. He was quiet for a minute as Dean flipped through the channels, snatches of Christmas specials and cooking snows whisking by like billboards through the window of a train. 

“Actually, Dean,” Sam began at last. “I wanted to talk to you about that.” 

“What, about me being a glorified toddler? Sorry Sam, my immaturity is here to stay.” 

“No, I mean about you living alone. Or more accurately, about you getting a roommate.” 

Dean shifted his gaze from the television to his brother, raising an eyebrow in askance. 

“Maybe you should at least think about it,” Sam suggested.

“Hang on,” Dean said, raising a finger. “Let me see: doing whatever I want, whenever I want; or, being stuck with some weirdo who washes his socks in the sink or organizes the fridge magnets by color. There, I thought about it. I’ve decided it’s a bad idea.”

Sam shrugged, a coy smile playing across his lips “That’s convenient.” 

If there was one thing that grated on Dean’s nerves, it was Sam being passive aggressive. He narrowed his eyes. “What’s that supposed to mean?” 

“Well, you’d have to sell your soul to Satan in order to actually get a roommate who wasn’t bound to you by blood, so writing off the entire concept is probably a good decision.” 

“Woah now,” Dean said, holding his hands up defensively. “I am a freaking joy to live with.” 

Sam smiled tiredly. “Dean, you routinely blast Metallica at three o’clock in the morning. And you drink straight from the milk carton. And you always put it back in the fridge even when it’s empty. And even when the milk goes bad, you never throw it out.” 

“Wow, I never knew that you were holding back so much milk-related anger,” Dean said drily. “Do we need to stop by our local farmer’s market for relationship counseling?” 

“Actually, it doesn’t really bother me,” Sam said, shrugging. “Like I said, you’re my brother. Dealing with each other’s crap is part of the job. But,” he said, raising his eyebrows and looking Dean dead in the eye, “if you had to get anyone else to room with you, you would be screwed.”

Dean met his gaze. “That sounds an awful lot like a challenge, little bro,” he said, not really sure why he was letting himself be drawn into this but at the same time not really caring. Sam held up his massive hands and tilted his head. 

“Guess that depends on whether or not you’re accepting it,” he said. 

“Why should I?” Dean shot back. 

“Well for one, it means I won’t get to mock you for backing down from a bet,” Sam clarified. 

“Oho, so we’re betting now,” Dean said with a grin, leaning forward and rubbing his hands together eagerly. “This just got interesting. What’s on the table?” 

Sam tapped his fingers against his lips thoughtfully. “Alright, try this on for size,” he said at last. “If you can find a roommate by the end of our Christmas party, I’ll cut my hair.” 

Dean’s eyes widened. “Seriously?” He’d been trying to get Sam to shave his luscious locks for years. He had fully resigned himself to having Rapunzel as a little brother up until now. 

Sam nodded sagely. “Seriously,” he agreed. 

Dean thought about it, turning the concept over in his head. It has been a while since Sam and he had done this sort of thing, and they might not get another opportunity for a long time now that Sam was moving out. Not to mention the fact that he could totally find a roommate in like five seconds if he wanted to. “What happens if I can’t?” he asked.

Sam grinned. “Losing confidence already?” he said. “That’s a bad sign.” 

“I’m just exploring my options,” Dean snapped, which just made Sam chuckle even more. 

“I’ll think of something I’m sure,” he said. “But hey, you shouldn’t have to worry about it, right? Finding a roommate should be totally easy for you.” Honestly, in that moment Dean would have walked on water just to wipe the stupid smirk off of Sam’s stupid face. 

“Yeah, it will be,” he said, leaning forward to shake his brother’s hand. “You might want to invest in some fashionable scarves. Because once all that hair is gone, your neck is going to be cold.”

“That was possibly the least intimidating threat I have ever heard,” Sam replied seriously.

 

\---

 

Dean spent the next week and a half before the oncoming party in alternating states of apathy, overconfidence, and unease. He hadn’t started making inquiries until three days after Sam had made the bet; he’d started out by going through his old college contacts, relatively sure that at least one of them would be in one state of poverty or homelessness suitable for finding a roommate. As it turned out, they were all either in varying states of unavailability or totally undesirable as people he’d be sleeping in the same house with.

Once his pool of college friends was exhausted he moved to high school friends, distant relatives, and people who he had only spoken to a maximum of three times. As his list of potentials grew shorter he started to doubt that Sam’s hair ever would. At one point he was about to seal the deal with an old drinking buddy, until he found out that the guy’s twelve cats were not up for negotiation. He considered opening a phone book and calling the first numbers his fingers hit, but Sam cheerily pointed out that if their numbers were listed then they already had an address. 

When he didn’t have the phone plastered to the side of his face, Dean felt like he was caught in a red, white and green tornado. If he stayed in one place for too long he was pretty sure he’d end up with wreaths around his neck. Sam had already stuck mistletoe at the top of every door, which Jess then used as an excuse to ambush her fiancé with sloppy kisses every time he entered a room. Dean was going to start losing his voice from gagging at them so much, but if there was one thing he was committed to it was, apparently, ruining Christmas. Yeah, on second thought Sam and Jess might have had a point about him needing to lighten up for the holidays. 

He ended up volunteering in the kitchen on the condition that he would make sure that at least 70% of the food made it to the party without being intercepted by his mouth. He churned out legions of gingerbread men, which Jess begrudgingly allowed him to decorate. He was actually pretty good; his large, rough hands might suggest otherwise, but working as a mechanic had taught his fingers to be nimble and precise when they needed to be. A good number of the cookie men ended up with fangs or frowny faces, but that was totally intentional and Jess let it slide.

Finally, the night of the party arrived and Dean was still without a single person willing to room with him. He was starting to seriously wonder if his living habits were really as obnoxious as Sam made them out to be. Well, he wasn’t overly worried about it. Whatever Sam had in store for him, it couldn’t be that bad. Dean had always been the imaginative one when it came to psychological warfare. He’d handcuff someone to the radiator at this point if that’s what it took. 

Luckily, the preparation for the party didn’t leave him a lot of time to worry about his situation. The air was buzzing with energy as he, Jess and Sam worked to set out vats of eggnog and spruce up the decorations for the hundredth time. If the excitement was beginning to catch on with Dean, well, he’d just tell himself that he was looking forward to the whole ordeal being over. Not like he wasn’t allowed to stand back and smile at the fruits of their hard work. It looked like someone had exploded a Christmas bomb all over their whole apartment. 

“Well, look who’s finally cracked a smile,” Sam said, sidling up beside him with a small glass of eggnog and a smirk. 

Dean shook his head. “You better help me clean all this up before you move out,” he said, his voice coming out a lot more sentimental than he had intended. 

Sam clasped his shoulder with a smile. “Of course, Dean.” 

Dean cleared his throat awkwardly, shuffling his feet. “I’m gonna miss you, you know,” he said. “And Jess. It’ll be weird, not having you guys around all the time.” Damn, he really had caught the Christmas bug. Sharing his feelings was really not something Dean Winchester made a habit of. 

“You’ll be fine,” Sam said with a smile. “Just think, you’ll never have to worry about walking in on us having sex again.” 

“God, don’t ever remind me of that,” Dean said darkly. Sam laughed. 

“Oh, by the way,” he said, the glint in his eyes turning absolutely evil. “How’s your search for a roommate coming? I would have thought you’d be strutting with a pair of shears by now.” 

“Actually, I haven’t had much luck,” Dean said, shrugging it off. “But whatever. I didn’t really want one anyways.” 

“Oh really? That’s too bad,” Sam said, and if he showed any more teeth Dean thought his mouth might actually stretch off his face. “Because I came up with my conditions of you losing the bet.” 

Suddenly Dean was feeling a lot less confident in the consequences of his failure. 

Sam drew it out for as long as possible, relishing the flicker of fear playing across Dean’s face. “You remember Garth, don’t you?” Sam asked. “Turns out he’s been looking to move to the city for a while. He was going to get a place over on fifth street, but when he hears that you have an open room I’m sure he’ll be thrilled to move in with you.” 

Okay. Dean took back everything he had ever said about Sam not excelling at psychological torture. 

“But hey, no worries right?” Sam said brightly, clasping Dean on the shoulder and refusing to comment on the shade of pale green he was probably going. “I’m sure you have this roommate thing in the bag. After all, you have until the end of the party. Who knows who’ll show up.” 

“You do, for starters,” Dean said, using his irritation to cover the rising tide of panic in his stomach. “A fact which you have constantly flaunted around in front of me for the past two weeks. Come on Sam, what do you know that I don’t?” 

Sam’s only response was to press a finger to his lips, to which Dean responded with an elbow in the ribs. Sam jabbed him in the stomach in response. 

“Play nicely, children,” Jess said as she strode into the room, her arms full of a bundle of fabric which she dumped onto the last remaining surface which wasn’t covered in decorations. As soon as her arms were empty, Dean was given a full view of what was possibly the ugliest Christmas sweater in existence. And seeing as there was no such thing as an attractive Christmas sweater, that was saying something. All his thoughts of Garth were banished in a haze of orange and grey wool.

“Oh my god, Jess,” he said, holding up his hands like a shield. “Not like I’d normally be staring at your chest or anything, but if I have to look at that sweater for five more seconds I’m going to gouge my own eyes out.” Sam slapped him upside the head for that comment, but Dean and Jess teased each other so often that he had long since given up on hounding him. 

“Don’t worry, I’ll be out of here in a second… as soon as you guys have put on these,” she said, reaching down to hold up one of the things she had been carrying; to Dean’s horror, it was a second, larger sweater, grey and woolen with at least five different patterns going on at once. It looked like the unholy offspring of a yak and a pine tree, knitted together by an old lady with dementia. 

“Hell no,” he decided, even as Sam was reaching out to take one with a reluctant expression on his face. 

“Don’t bother fighting it, Dean,” he said, pulling the thing over his head. 

“Not happening,” Dean said. “Absolutely no way. One hundred percent never.” 

And then Jess did the worst thing she could have done. She smiled. 

“Is that so?” 

 

\---

 

Like it wasn’t bad enough that Dean was shoved into this ridiculous sweater, and facing down the possibility of sharing an apartment with Garth, but Jess had also put him on door-answering duty. Penance for attempting resistance, no doubt. Well, Sam had warned him. He had been horrified to discover that the back even had sequins, but at least they were out of his line of vision.

In the minutes before the party was due to start, he went over his options. It wasn’t like he hated Garth or anything; he was a good guy, and Dean liked him, but he liked him even better when he was at least ten yards away from him. The thought of living with the guy was enough to make him start weighing the benefits of fleeing the country. Because there was no way that his last act as Sam’s roommate would be backing out of their bet. 

The way Dean saw it, he had one chance: he would have to find someone at the party to be his roommate, or suffer the consequences. 

The doorbell rang for the first time at two minutes after seven. Dean opened the door on Bobby and Jody, their eyes creasing with smiles when they saw him.

“Boy, that is the ugliest damn piece of clothing I have ever seen,” Bobby grumbled, stepping in to wrap Dean up in a gruff hug. 

“I think it’s festive!” Jody chimed in, stepping in to peck Dean on the cheek as soon as Bobby stepped away. “Hiya Dean. How are you?” 

Dean couldn’t stop himself from grinning. He never could around those two. “I’m doing okay,” he said. “Don’t suppose either of you know anyone who’s looking for an apartment?” 

They book shook their heads, and Dean shrugged. “Ah, didn’t think so,” he said lightly, beckoning them forward. “Come on in. There’s enough eggnog to knock even you under the table, Jody.” 

“We’ll see about that,” she said, her eyes gleaming, and Bobby laughed. 

“No, we won’t,” he protested as he followed her into the apartment. 

From then on the guests came at a steady flow: Becky dragging a bedraggled Chuck in her wake and Rufus sidling in with his trademark bottle of liqueur. Pamela breezed by with a wink and a pat on Dean’s ass, while Adam got by with a grin and a punch to the shoulder. Andy nearly tripped over the welcome mat and brained himself on the door frame, but Dean managed to get him inside without any further injury. Ellen and Ash arrived together with the promise that Jo would be along shortly, and Dean spent a long time catching up from the years that had passed since they’d last met up. Even Crowley’s weird family or commune or coven or whatever it was showed up, although he swore Ruby gave him the stinkeye as she and Meg walked by. Apparently Sam and Jess’s guest list was more inclusive than he would have expected. 

No one he talked to needed a roommate, and a few of them he had already asked. By the time seven-thirty rolled around he was resigning himself to an existence of manic optimism when suddenly the doorbell rang again. Drawing himself up out of the armchair he had sunken into, he trooped up to answer it for what would hopefully be the last time. Dean had given up on guessing who was coming a long time ago, but at this point he was pretty sure he was incapable of being surprised. 

As it turned out, he was wrong. 

“Zach?” he gaped, staring at the older man standing loosely in his doorway like he was an alien species on his doormat. 

“That’s Doctor Novak to you,” he said snidely, shuttering Dean out of his way with a swipe of his cane. Of course he would have a cane. The dude was like an evil oil baron ripped right out of the pages of some crappy drugstore novel, and he was now standing in the foyer of Dean’s apartment. 

“Sam invited you? Seriously?” Dean probably should have been a bit more polite, but he was confused and honestly wouldn’t have cared anyways. Zach just gave him that trademark slimy smile and shrugged off his coat. 

“He did indeed. The rest of the gang will be up in a minute, so be sure to greet them with the same slack-jawed expression. Yes, that’s the one. Put this somewhere, will you?” He shoved his coat into Dean’s arms and waded into the party without another word. 

Dean resisted the impulse to go stuff the bastard’s coat into the toilet, dumping it in the closet and setting off to find Sam instead. He caught his brother chatting with Andy over the punch bowl and dragged him into a slightly quieter corner. 

“You invited the Novaks?!” Dean hissed. In high school Dean had had the most insane crush on Anna Novak. The first time he had visited her house had been for her birthday party, during which Dean planned on seeing if he couldn’t cut himself a slice of that metaphorical birthday cake. That had been before he had accidentally dropped the much more literal cake all over her younger brother Castiel. The whole thing had turned into a long-running joke in Anna’s household. The memory still made him cringe. Not to mention the fact that he later found that Anna didn’t swing that way.

Sam, of course, looked like he had just won the million-dollar lottery. “Yeah Dean, we’ve been close for a while. Balthazar was in my Chem class, although I’m pretty sure he spent more time mixing cocktails than compounds. The whole family is coming out to visit for the holidays, and I thought it would be good to catch up.” 

Dean groaned, pressing the heels of his hands to his eyes. “Dude, so not cool. You know there are about fifty reasons why Anna wouldn’t be interested in me, chiefly among them the fact that I do in fact have a penis.” 

“Anna’s engaged, Dean,” Sam said with a secretive smile. “But don’t worry. She has lots of siblings. Speaking of which…”

Dean turned to see Jess ushering in a crowd of people, shaking the snow off their various winter coats and smiling brightly at the décor. Dean recognized Anna instantly; he’d know that red hair anywhere, though she’d cropped it short since he’d seen her last. A few of her siblings he recognized, and even more he didn’t—he’d had no idea that Anna’s family was so huge. 

Before he could protest Sam was sweeping him up towards them, a firm hand on his shoulder stopping him from squirming away. 

“Damnit Sam, I don’t want—” he growled, but then he was deposited face-to-face with Anna.

She was talking to Jess, but as soon as she saw Dean her eyes widened in surprise. Dean braced himself for an awkward bout of small talk or maybe even some lingering resentment over the whole cake incident, but to his surprise she broke out into a broad grin and wrapped him in a warm hug.

“Dean!” she cried, pulling back to inspect his face with a wide smile before giving Sam the same treatment. “And Sam too! It’s been such a long time since I’ve seen you guys!” 

“Anna, hey,” Dean replied, more than a little thrown off. “I know, it’s been years. How have you been?” Being around Anna again didn’t feel nearly as weird as he expected it to. He’d forgotten that his infatuation had been based on more than her looks. Not like he still had a crush or anything. It was just nice to see that she was still genuinely a good person. 

“I’ve been great,” she said, her smile practically luminous. “Just got my medical license, actually.”

Dean whistled appreciatively. “Wow, congratulations. That’s a really big step. Hey, speaking of which, Sam told me you got engaged?” 

She smiled shyly. “Yeah, he told you right.” 

“That’s great,” Dean said, and he really meant it. “When do I get to meet the lucky chump?” 

Anna’s smile widened. “Well, now that you mention it…” she craned her neck around and reached into the chattering mob behind her to pull out none other than Jo Harvelle, who slid an arm around Anna’s waist with a twist of her lips. 

“Hey Dean,” she said. 

Dean shook his head, an enormous grin dawning on his face. “Oh, no way,” he said, stepping forward to pull them both into a tight hug. “You guys. Wow.” Suddenly he pulled back and punched Jo lightly in the arm. “I can’t believe you didn’t tell me about this sooner!” 

Jo laughed and shoved at him playfully. “I wanted it to be a surprise,” she said. “So, surprise!” 

“Surprise is right,” Dean said with a playful grin. “If anyone told me you were going to bag a smart, beautiful doctor wife I would have laughed myself under the table.” The playful insult was set off a bit by the fact that he couldn’t stop smiling. Jo leaned in to kiss Anna’s cheek fondly, and Dean was too happy to tease them for being sappy.

“You’re telling me,” she said. “I suspect that something supernatural is at play.” 

“Oh, shut up, you,” Anna said, squeezing Jo’s arm fondly before turning back to Dean. “If you don’t mind I’m going to go say hi to Ellen. I’m sure she’ll want to make sure I’m treating her baby girl right.”

“That’s fine,” Dean said with a smile. “You two take care. And you better invite me to the damn wedding.” Taking Anna by the hand, Jo guided her into the crowd of people milling around the rest of the apartment. 

“Well, that was appropriately tiresome,” a bored, British voice said from his side. Dean turned back to find a man in a ridiculously low cut v-neck ambling up to him, a small glass of eggnog held loosely in his fingertips. Dean raked his memory for a name that he knew was there.

“It’s Balthazar, right?” Dean ventured. He vaguely remembered that aura of pretentiousness paired with a stupid name from his time back in high school.

“Bravo,” the man replied with a smirk. “You must be Dean Winchester. Notorious wielder of birthday confections.” 

Dean was really starting to remember why he hated parties so much. 

“Come along now,” Balthazar said, waving vaguely at his sleeve like he was going to tug on it but didn’t want to dirty his hand. “Our dear Anna has asked me to introduce you to the rest of the family. Now, that sounds like a lot of work, so I’m just going to leave you with Micheal.” 

With little other choice, Dean followed in Balthazar’s wake, wondering if douchey-ness ran in Zach’s family. By the time the other man pulled to a stop in front of a large knot of people, Dean had thought up five different ways to excuse himself and ordered them by degrees of profanity. He figured he could make it to the fire escape from his room and spend the rest of the night bouncing around from one bar to another until he was sure the apartment wouldn’t be full of people itching for a chance to dig up embarrassing high-school stories. 

And then he saw him. 

The man was standing on the fringe of the little group, his shoulders slumped under the fabric of his trench coat. He had messy black hair and a jawline you could wreck a freakin’ ship on, and when he met Dean’s eyes he just stared. Dean couldn’t remember the last time that just looking at someone had made him feel like the air had been punched out of his lungs. Well, fuck. This wasn’t supposed to happen. 

“Idiot delivery,” Balthazar drawled, snapping Dean’s attention away as the other man turned on his heel to disappear back into the crowd. A tall man with neatly parted dark hair was standing in front of him, his eyes sharp but kind. 

“Sorry about ‘Zar,” he said with an apologetic smile. “At this point we’ve given up on convincing him to behave like a decent human being.” The man extended his hand. 

“I’m Michael,” he said, grasping Dean’s palm firmly. “I don’t think we’ve met; I was at college when you knew Anna.” 

“Nice to meet you,” Dean said evenly. 

“Let me properly introduce the rest of the Novak clan. I’d be surprised that you remembered Balthazar’s name, but then again he makes it hard to forget.” Dean smiled ruefully at that. 

“Alright, there’s Luc, oldest after me—” Michael said, gesturing to a tall man with dirty-blond hair and a cool smile. “—Gabriel, the troublemaker—” he said, as Gabriel shot him a wicked grin; “our cousin Raphi, the lawyer in the family—” she bobbed her head in acknowledgement;“—You’ve already know Balthazar and Anna,” Micheal continued, “And, uh,” he fought down a smile as he gestured to the last man, the one that Dean had been trying so hard not to look at, “I think you and Castiel have made each other’s acquaintance.” 

Dean’s jaw practically hit the floor. That was Castiel? Was that even possible? Dean remembered him as a gangly, thin guy with messy hair, glasses, and a conservative taste in clothes. The man standing in front of his now was as far from that memory as possible. 

He’d fleshed out, for one. Stringy muscle had turned lean, making his body compact like a runner’s. His glasses were gone, leaving nothing between Dean and the intense blue gaze he fixed him with. The peach fuzz on his teenage face had turned to rough stubble that looked about ten billion times better than Dean remembered. The only thing that had stayed the same was that messy head of hair. 

A tiny smile played across Castiel’s lips as Micheal introduced him, and he must have seem the horror-struck expression on Dean’s face before he fought it down. 

“Hello, Dean,” he said, and fuck, had his voice always been that low? 

It was only when Gabriel cleared his throat obnoxiously that Dean realized he was staring again. He forced himself to make eye contact with the rest of them, hoisting a smile.

“Nice to see you,” Dean said. “All of you,” he amended, suddenly remembering that there were six other people in the room that he had been unintentionally ignoring. What the hell was wrong with him? He could have sworn that Luc was smirking, but maybe he was looking into it too much. He stepped back and coughed awkwardly, gesturing towards the rest of the party. 

“Feel free to mingle,” he said, painfully aware of how awkward he was being. Thankfully the Novaks began flitting away into the crowd before he could do anything even worse. Gabriel winked at him on the way by before making a beeline for the sweets table. Castiel caught his gaze for a beat longer before shuffling off in a seemingly random direction, his movements careful and calculated. He hadn’t even taken his coat off. 

Well shit. 

Of course it had to be Castiel. Out of all the people, it had to be the one he had smeared cake all over in the tenth grade. Was he intentionally undermining himself? Besides being attractive to an ungodly level, Castiel was undoubtedly a brainiac; practically everyone in his entire family was a doctor, and why should he be any different? The guy was out of Dean’s league at every bracket, and that normally wouldn’t even occur to him. Yet still Dean found himself sidling off in the direction he had seen him leave. 

It’s not stalking, Dean told himself as he trailed after the other man vaguely. It’s my house, my party. I’m just walking around in my house. Oh look, there’s that guy in the trench coat again. What a coincidence. 

“Hey Dean.” He practically leapt out of his skin as Sam appeared out of nowhere, a glass of eggnog in his hand and a giant, goofy grin on his face. “Enjoying the party?” 

“Yeah, Sam, it’s fine,” Dean said distractedly, his eyes raking the sea of faces and bodies for the one he was looking for. 

“That’s good. Enjoy yourself while you can,” Sam said, and his grin was positively criminal. He tapped his watch. “Tick tock, Dean.” Before Dean could make a retort his little brother had shuffled his way back into the crowd. By that point Castiel had also conveniently disappeared. Dean should probably take that as a sign, but the party was so small that he couldn’t help but run into him again. And once that happened, he doubted he’d be able to stop himself from talking. So he resolved not to bother trying.

He finally caught up with the guy around the food table, where Castiel was neatly arranging a series of gingerbread men around the edge of his plate. Dean was about to step up to him when he faltered. What was he supposed to say? ‘Hey, haven’t seen you since highschool, and I find you very attractive, and by the way sorry for dumping a cake over your head and making us both a laughingstock’?

“Perhaps you should stand back.” Dean was jerked out of his reverie by that same gruff voice, and with a thrill of horror he realized Castiel was talking to him. 

“Sorry, what?” he asked, his voice slightly strangled. That same smile toyed with the edges of Castiel’s mouth in a way that Dean refused to find fascinating. 

“I said, perhaps you should stand back,” he repeated. When Dean continued to look confused and slightly terrified, his smile widened. “Unless you think you can trust yourself around me in the vicinity of so many pastries.” 

Dean’s eyes widened and he found himself laughing before he even realized it. 

“I was, uh, hoping you’d forgotten about that,” Dean said, rubbing the back of his neck. 

“My siblings made that largely impossible,” he commented drily, lifting a cookie man to bite off its head. It took every ounce of willpower for Dean not to stare at his mouth. What the fuck was wrong with him? 

“If it’s any consolation, I still feel like shit about it,” Dean murmured. 

“And if it’s any consolation, I wouldn’t want you to. It’s all in the past.” 

Dean smiled hesitantly. “Well, I’m glad to hear that.” He shuffled his feet awkwardly, not really sure what to say. He was generally awesome at flirting, but he was also generally flirting with strangers at the bar that he had never seen before and would probably never seen again. Castiel and him already had history, even if that history was near-ancient and smelled faintly of raspberry frosting. 

“So what have you been up to?” he asked, because it seemed like a safe enough question. 

“I was recently accepted into masters program at the School of the Art Institute of Chicago,” Castiel said with the same tone of voice that he might have used to comment on the weather. 

“Wow. Okay,” Dean said. To be honest, he had been expecting med school. “That’s pretty awesome.” 

“It is a relief to have the application processes over with,” Castiel admitted, studying Dean carefully with those ridiculously blue eyes. “And yourself? What have you been doing since high school?” 

Dean smiled painfully. “Well when you open with getting accepted to a prestigious university, it’s kind of hard to top that.” 

“I wasn’t aware that it was a competition.” 

“Oh come on, Cas, it’s always a competition,” Dean said lightly. “When you meet someone from high school it’s always a test to see who’s done better for themselves. Just the rules of life.” 

“Ah.” Castiel frowned. “I was not aware of that.” 

Dean looked at him shrewdly. Apparently years of schooling had done little for Castiel’s social skills. Then again, if Dean had spent the last five years studying he’d probably be talking like a textbook as well. 

“Always,” he said, waving it off. “If this was a competition, you would win hands down. I did some college, but it didn’t really stick. I ended up dropping out and working in an auto shop.” He shrugged. “I may not be saving lives, but it’s good work and I like it.” Dean wished he didn’t feel the need to defend himself to Castiel, but it was hard not to. He wanted to present some facet of himself that Castiel would find interesting, but couldn’t seem to stop fumbling.

“You always had a penchant for cars, if memory serves,” Castiel was saying. “There was that black car that you always drove everywhere once you got your license.” 

“The impala,” Dean said automatically. “Yeah, that’s right. How did you remember that?” 

Castiel grins offhandedly. “Every day after school I had to wait on the curb after band practice. You made a point to floor the accelerator whenever you left the parking lot.”

“I’d forgotten about that,” Dean said with a smile. “And I didn’t know you were in the band. What did you play?” 

“Flute,” Castiel said. 

“Were you any good?”

“Quite terrible, actually. During concerts our conductor would often tell me to just pretend that I was playing.” 

Dean laughed. “What a dick. Professor Grene, right? Didn’t that guy also teach calculus?” 

“I believe so,” Castiel said with a nod. “Although I am not sure how he managed to get two positions with such little overlap between them.” 

“Definitely might explain why he sucked so bad at both,” Dean replied. The pair exchanged a grin. 

From there things went surprisingly well. They talked about old high school teachers, ones they hated and ones that made school a little less bearable; Dean discussed his different methods for sneaking out of school, and Castiel admitted that he had regularly gone to the nurse to avoid going to art class. They drifted around the party, occasionally meeting with other people to chat before pulling away on their own separate orbit. By the time the party was wearing down Dean was hauling up memories he hadn’t thought about for years, stuff he didn’t even know he still remembered. He liked it when he could make Castiel laugh, or even just smile. God, he was hopeless. And to think he mocked Sam for his sappiness. 

“No way,” Dean was saying, keenly aware of the fact that many of the guests were starting to leave. “I didn’t know you were in my astrology class.” 

“I sat in the back,” Castiel explained. “I didn’t volunteer much either. But I have to say, it was one of my favorite classes.” 

“Confession time: I never actually did any of the star gazing,” Dean admitted. “I just looked up star maps on Google and copied from there.” 

Castiel looked genuinely disappointed. “The star gazing was my favorite part,” he said. “I dug an old ladder out of my family’s shed and used it to climb on the roof, unbeknownst to my father. I’m sure he would have had something to say about that if he had noticed.” Dean picked up a bitter note in Castiel’s voice at that. Out of the corner of his eye he could see that the room was nearly empty, except for a few stragglers around the punch bowl and of course the majority of Cas’s family. Soon, Castiel would have to leave, and Dean would have to stop deluding himself that the other man found him anything other than a tiresome distraction. But until then… 

“Hey, tell you what,” he said. “Are you a believer in ‘better late than never’?” 

“That depends on what you’re suggesting,” Castiel said cautiously. 

Dean smiled. “If you don’t mind a little climbing, the fire escape can get us to the apartment’s roof. Maybe we can see some stars from there.” 

Castiel wavered, and for a second Dean thought he was going to turn him down. But then he looked up and a big, conspiratorial grin spread across his face. “Alright, let’s do that,” he said, glancing around to see if the other members of his family were around. Dean lead him over to the door to his bedroom and slipped inside when he was sure no one was watching. Ignoring the part of him that was screaming about him and Castiel being alone in proximity to a bed, he crossed the room and pulled open the window that lead to the fire escape outside. Grabbing an extra jacket from his closet, he climbed out and beckoned for Castiel to follow. 

“I am starting to think this is less than a good idea,” Castiel said nervously as he clambered out onto the rickety metal structure and peered at the long drop below. Dean grabbed his arm to keep him steady with a smile. 

“Don’t worry, Cas,” he said. “I’m not gonna let you fall.” 

They made their way up the stairs, keeping a firm grip on the railing where they could, until they made it up to the roof. It took some maneuvering to convince Cas to climb his way up there, but after some coaxing they both made it up. 

Of course, the problem then became the fact that there wasn’t a star to be seen in the sky. A thick layer of clouds hung low in the sky, reflecting the lights of the Chicago skyline in a sickly orange glow. The only lights up there were from the occasional airplane. 

Dean grinned ruefully. “Sorry, Cas,” he said. “All that effort, and not a star to show for it.” 

“It’s alright,” Castiel said. “It’s nice being up here, actually. I wouldn’t mind staying for a while, if you don’t mind. The fresh air is nice.” 

“Not at all,” Dean said, sitting down on the concrete and patting the space beside him. “Pull up a slab.” 

Castiel lowered himself carefully to the ground, arranging his coat around himself like folding wings. Dean liked that image. 

“So, art school,” he said conversationally after a quiet moment of staring at the sky. “Decide to break out of the family’s doctor mold?” 

“Something like that,” Castiel said. “I never could imagine myself being a doctor. Although I often tried.” 

“Why not?” Dean asked. “I mean, you don’t have to tell me. Sorry. I’m just curious.” 

Castiel crossed his arms over his chest and rubbed his arms for warmth. “It’s a rather complicated rationale,” he admitted. “I want to create things. I want to make people think. My father always believed in the importance of keeping the body healthy, but art can heal the mind.”

“That’s a good way of thinking about it,” Dean said. “And how does your dad feel about that?”

Castiel’s face darkened. “My father believes I am wasting my time colossally. Micheal agrees, although the rest of my family is more supportive. But although I’d obviously prefer them to approve, in the end it doesn’t matter.”

Dean raised his eyebrows. “Why not?”

Castiel stared at him. “Everything doesn’t have to revolve around what other people think of you, Dean,” he pointed out. “As long as you’re happy, that’s what matters.” 

“Really?” he said with a grin. “Because I could have sworn you didn’t look too happy when everyone was laughing at all the cake on your shirt.” 

“If you keep bringing it up, I might just have to exact some form of revenge,” Castiel warned him, a smile in his eyes. 

“You don’t seem the type to be all that good at pranks, Cas,” Dean commented. 

“Oh, I would be quite terrible,” he said cheerfully. “But I promise you would at least get a good laugh out of it.” 

“I’m laughing now,” Dean chuckled. It didn’t take long for Castiel to join him. Their breaths puffed out in thick clouds of condensation, making Dean glad he had thought to bring another coat. Despite the cold, though, he was much more comfortable up here than he had been down at the party. It wasn’t like he had forgotten how ridiculously attractive Castiel was by any means, but there was more to it than that. They got along so well.

“I am looking forward to living in this area,” Castiel mused, pulling his knees up to his chest with a sigh. “As much as I love my family, some time away from them will be a relief. More accurately, it will stop me from checking myself in to a mental institute.” 

“Yeah,” Dean said uncertainly, immediately thinking of Sam and his imminent departure. “I don’t know. All family’s not so bad.” 

“Yes, of course. You do live with your brother.” Castiel shuddered. “I can’t imagine doing so myself. Don’t you ever drive each other crazy as siblings do?” 

“Oh yeah, all the time,” Dean said with a wry smile. “But I’ve lived with him for all of my life. It’s going to be weird not having him here. I don’t want him to forget me or whatever.” 

Castiel smiled. “Well, that is the wonderful thing about family, isn’t it? No matter how far away they are, you can always be close. Consequently, that is also the awful thing about family,” he said darkly. When Dean shot him a strange look, he shook his head. “If you knew Gabriel better, you’d understand.” 

Dean laughed. “Hallmark aside, you do have a point. I know I’m just being paranoid about Sam, but it helps to hear someone else say it. So thanks.” 

“It’s nothing,” Castiel said. They sat in a comfortable silence for a while, staring out over the clouds and buildings below. 

“So, where are you staying?” Dean asked. “I’m guessing you’re a bit beyond the dorm-room stage at this point.” 

“I would sooner live in a cardboard box than return to living in the dorms,” he said. “Although I have yet to find a place to stay.”

“Do you want to room with me?” It took Dean a second to realize that he had in fact asked that question, and then it was a second longer before he could process how to backpedal. “I mean, I do have a room open,” he fumbled, quickly looking away. “Just thought I’d offer, this was stupid, forget I said anything.” 

Castiel was quiet, and refused to stop looking at him. Dean in turn made sure to look anywhere except at Castiel, studying the thick fuzzy ceiling of clouds where the stars were supposed to be. Smooth, Winchester. Very smooth. Since when was he this awkward, let alone this clingy? It was like having Castiel here was raising all his high school insecurities from the grave. 

“Actually,” Castiel said after a long, thoughtful pause. “If you truly are offering…” 

Dean’s eyes zipped back to Castiel’s face like iron shavings to a magnet. “Wait, really?” he said, unable to keep the hope out of his voice. “I mean, no pressure or anything. Don’t feel obligated.” 

Castiel smiled. “I’m saying that out of a sense of obligation, Dean,” he said, in a way that made Dean’s heart beat faster. “I’m saying that because I like you.” His eyes lingered on Dean for a long time.

“Oh.” Dean’s face split into a smile. “Well, that’s great. You’re not so bad yourself.” 

“Not to mention you owe me a night of stargazing,” he said warmly. The part of himself that was capable of believing that this was really happening couldn’t agree to that soon enough.

Castiel glanced at his watch with a frown. “We should probably get back soon,” he said regretfully, glancing around. “Although…would you mind if we stayed up here a bit longer?” 

“No problem at all, Cas,” Dean said, leaning back on his hands and wondering how this night ended up turning out so perfectly. 

“Thank you,” Castiel said sheepishly. “Because I don’t think I can climb down.” 

 

\---

 

When Dean finally got Cas off the fire escape and back into the apartment, he found that the rest of the Novaks were waiting for him. Sam looked apologetic when he wasn’t shooting Dean meaningful looks behind Cas’s back. 

“Well, well, Cassie,” Balthazar said, sidling up to clap him on the back. “I see you found yourself an alternative to party games.” Castiel ignored him. 

“There you are,” Micheal said, beckoning Cas over. “Come on, Cas. We need to get back to the hotel.” 

“Yes, of course,” Castiel said, pulling his coat tighter around him and turning to face Dean. After a not-so-brief moment of eye contact he extended his hand, a card gripped between his fingers. 

“Contact me as soon as you wish about the apartment,” he said, stoicly ignoring the muffled giggles from Gabriel behind him. Dean accepted the card without reading it, reaching out to shake Castiel’s hand. His palms were smooth and broad.

“I will,” he said. “I’m really glad you came here tonight, Cas. I uh, I think this is going to be great.” 

“I have a feeling you may be right,” Castiel said with a smile. “I will speak with you later, Dean Winchester.” 

“Count on it.” With one last bob of his head, Castiel followed the rest of his family out the door and closed it behind him with a soft click. A second later Dean turned around, a giant grin plastered on his face. 

“Better get the scissors, because I just found a roommate,” he crowed. Sam didn’t look nearly as horrified as Dean had expected him to; actually, he looked pretty pleased with himself. Dean narrowed his eyes. 

“You look awfully happy for someone about to get sheared,” he said suspiciously. Sam shrugged. 

“I’m just happy you found a roomie is all,” he said casually. Too casually.

Dean’s jaw dropped. “Were you planning this?” he said in disbelief. “The whole time, talking about who was coming…” 

“Merry Christmas, Dean,” Sam said, clapping him on the shoulder happily. “And before you going second-guessing your way into screwing this up: yes Castiel is interested, and no, I didn’t make a deal with a demon to make this happen.” 

Dean shook his head. “Is this really a good idea?” he asked, sinking into a chair. “I mean, we haven’t seen each other in years. What if we end up hating each other?” 

“Then he can move out,” Sam replied simply. “Trust me, Dean. Anna and I have been planning on introducing you two for a while.” 

“Wow, Sammy,” Dean said, trying to hide the smile on his lips. “Your scheming continues to amaze and disturb me.” 

“If it’s any consolation, the thing with Garth was Anna’s idea,” Sam said, flopping down on the couch. Dean eyed him out of the corner of his eyes. 

“Well, I guess I owe you a thank you,” Dean said. Sam mock-bowed with a flourish, and Dean broke into an evil grin. 

“But don’t think this means you’re backing out of your haircut.”


End file.
